US8658642B2ActiveUtilityA1
Arylsulfonamide CCR3 antagonists
Est. expiryApr 22, 2029(~2.8 yrs left)· nominal 20-yr term from priority
A61P 37/06A61P 37/00A61P 35/02A61P 43/00A61P 9/00A61P 37/02A61P 37/08A61P 25/28A61P 27/14A61P 29/00A61P 27/02A61P 11/00A61P 17/00A61P 19/02A61P 11/06A61P 17/06A61P 17/10A61P 1/04A61P 17/02A61P 17/04A61P 11/02A61K 31/496C07D 261/08A61K 31/5377C07D 231/12C07D 295/26C07D 213/50A61K 31/495A61K 31/497C07D 241/12C07D 333/22C07D 285/06A61P 1/00
48
PatentIndex Score
0
Cited by
32
References
36
Claims
Abstract
Provided herein are arylsulfonamides that are useful for modulating CCR3 activity, and pharmaceutical compositions thereof. Also provided herein are methods of their use for treating, preventing, or ameliorating one or more symptoms of a CCR3-mediated disorder, disease, or condition.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. A method for the treatment or amelioration of one or more symptoms of asthma, allergic asthma, exercise induced asthma, allergic rhinitis, perennial allergic rhinitis, seasonal allergic rhinitis, atopic dermatitis, conjunctivitis, allergic conjunctivitis, eosinophilic bronchitis, eosinophilic gastroenteritis, allograft rejection, chronic obstructive pulmonary disease, COPD (chronic obstructive pulmonary disorder), arthritis, rheumatoid arthritis, psoriatic arthritis, or osteoarthritis in a subject, which comprises administering to the subject the compound of Formula I:
or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, a tautomer, or a mixture of two or more tautomers thereof; or a pharmaceutically acceptable salt, solvate, hydrate, or prodrug thereof;
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently (a) hydrogen, halo, cyano, nitro, or guanidine; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; or (c) —C(O)R 1a , —C(O)OR 1a , —C(O)NR 1b R 1c , —C(NR 1a )NR 1b R 1c , —OR 1a , —OC(O)R 1a , —OC(O)OR 1a , —OC(O)NR 1b R 1c , —OC(═NR 1a )NR 1b R 1c OS(O)R 1a , —OS(O) 2 R 1a , —OS(O)NR 1b R 1c , —OS(O) 2 NR 1b R 1c , —NR 1b R 1c , —NR 1a C(O)R 1d , —NR 1a C(O)OR 1d , —NR 1a C(O)NR 1b R 1c , —NR 1a C(═NR 1d )NR 1b R 1c , —NR 1a S(O)R 1d , —NR 1a S(O) 2 R 1d , —NR 1a S(O)NR 1b R 1c , —NR 1a S(O) 2 NR 1b R 1c , —SR 1a , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c ;
R 7 is (a) halo, cyano, nitro, oxo, or guanidine; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; or (c) —C(O)R 1a , —C(O)OR 1a , —C(O)NR 1b R 1c , —C(NR 1a )NR 1b R 1c , —OR 1a , —OC(O)R 1a , —OC(O)OR 1a , —OC(O)NR 1b R 1c , —OC(═NR 1a )NR 1b R 1c , —OS(O)R 1a , —OS(O) 2 R 1a , —OS(O)NR 1b R 1c , —OS(O) 2 NR 1b R 1c , —NR 1b R 1c , —NR 1a C(O)R 1d , —NR 1a C(O)OR 1d , —NR 1a C(O)NR 1b R 1c , —NR 1a C(═NR 1d )NR 1b R 1c , —NR 1a S(O)R 1d , —NR 1a S(O) 2 R 1d , —NR 1a S(O)NR 1b R 1c , —NR 1a S(O) 2 NR 1b R 1c , —SR 1a , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c ;
X is O or S;
R Ya is —C(O)R 1a , —C(O)OR 1a , —C(O)NR 1b R 1c , —C(S)NR 1b R 1c , —C(S)NR 1a C(O)NR 1b R 1c , —C(NR 1a )NR 1b R 1c , —C(NNO 2 )NR 1b R 1c , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c ; with the proviso that R Ya is not —C(O)O-t-butyl;
m is an integer from 0 to 3;
n is an integer from 1 to 3;
p is an integer from 0 to 4; and
each R 1a , R 1b , R 1c , and R 1d is independently hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, or heterocyclyl; or each pair of R 1b and R 1c together with the N atom to which they are attached independently form heteroaryl or heterocyclyl;
with the proviso that the compound is not 4-(2-(3,5-dimethylphenoxy)-5-nitrophenylsulfonyl)piperazine-1-carbaldehyde; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heterocyclyl, and heteroaryl is optionally substituted with one or more groups, each independently selected from (a) cyano, halo, and nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, and heterocyclyl, each optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Q; and (c) —C(O)R a , —C(O)OR a , —C(O)NR b R c , —C(NR a )NR b R c , —OR a , —OC(O)R a , —OC(O)OR a , —OC(O)NR b R c , —OC(═NR a )NR b R c , —OS(O)R a , —OS(O) 2 R a , —OS(O)NR b R c , —OS(O) 2 NR b R c , —NR b R c , NR a C(O)R d , —NR a C(O)OR d , —NR a C(O)NR b R c , —NR a C(═NR d )NR b R c , —NR a S(O)R d , —NR a S(O) 2 R d , —NR a S(O)NR b R c , —NR a S(O) 2 NR b R c , —SR a , —S(O)R a , —S(O) 2 R a , —S(O)NR b R c , and —S(O) 2 NR b R c , wherein each R a , R b , R c , and R d is independently (i) hydrogen; (ii) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl, each optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Q; or (iii) R b and R c together with the N atom to which they are attached form heterocyclyl, optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Q;
wherein each Q is independently selected from the group consisting of (a) cyano, halo, and nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, and heterocyclyl; and (c) —C(O)R e , —C(O)OR e , —C(O)NR f R g , —C(NR e )NR f R g , —OR e , —OC(O)R e , —OC(O)OR e , —OC(O)NR f R g , —OC(═NR e )NR f R g , —OS(O)R e , —OS(O) 2 R e , —OS(O)NR f R g , —OS(O) 2 NR f R g , —NR f R g , —NR e C(O)R h , —NR e C(O)OR h , —NR e C(O)NR f R g , —NR e C(═NR h )NR f R g , —NR e S(O)R h , —NR e S(O) 2 R h , —NR e S(O)NR f R g , —NR e S(O) 2 NR f R g , —SR e , —S(O)R e , —S(O) 2 R e , —S(O)NR f R g , and —S(O) 2 NR f R g ; wherein each R e , R f , R g , and R h is independently (i) hydrogen; (ii) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; or (iii) R f and R g together with the N atom to which they are attached form heterocyclyl.
2. The method of claim 1 , wherein R Ya is —C(O)R 1a , —C(O)NR 1b R 1c , —C(S)NR 1b R 1c , —C(S)NR 1a C(O)NR 1b R 1c , —C(NNO 2 )NR 1b R 1c , or —S(O) 2 R 1a .
3. The method of claim 2 , wherein R 1a is (a) hydrogen; (b) C 1-6 alkyl, optionally substituted with one, two, or three substituents, each of which is independently selected from cyano, halo, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, heterocyclyl, —C(O)R a , —C(O)OR a , and —SR a , where the cycloalkyl, aryl, heteroaryl, and heterocyclyl are each further optionally substituted with one, two, or three substituents, each of which is independently halo or C 1-6 alkyl; (c) C 1-6 alkenyl, optionally substituted with C 6-14 aryl; (d) C 3-7 cycloalkyl, optionally substituted with one or two C 1-6 alkyl; (e) C 6-14 aryl, optionally substituted with one, two, or three substituents, each of which is independently selected from halo, nitro, cyano, —C(O)R a , and C 1-6 alkyl, where the alkyl is further optionally substituted with one, two, or three halo; (f) heteroaryl, optionally substituted with one, two, or three substituents, each of which is independently halo or C 1-6 alkyl; or (g) heterocyclyl.
4. The method of claim 2 , wherein R 1a is (a) hydrogen; or (b) C 1-6 alkyl, C 2-6 alkenyl, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, or heterocyclyl, each optionally substituted with one or two substituents, each of which is independently selected from halo, cyano, nitro, C 1-6 alkyl, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, heterocyclyl, —OR a , —SR a , and —C(O)R a , where the alkyl, cycloalkyl, aryl, heteroaryl, and heterocyclyl are each optionally further substituted with one or two substituents, each of which is independently halo or C 1-6 alkyl.
5. The method of claim 2 , wherein R 1a is (a) hydrogen; or (b) C 1-6 alkyl, C 2-6 alkenyl, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, or heterocyclyl, each optionally substituted with one or two substituents, each of which is independently selected from fluoro, chloro, cyano, nitro, methyl, trifluoromethyl, ethyl, methoxy, ethoxy, methylthio, (1S,2S,4R)-7,7-dimethylbicyclo[2.2.1]-heptyl, phenyl, chlorophenyl, furanyl, morpholinyl, acetyl, propionyl, and ethoxycarbonyl.
6. The method of claim 4 , wherein R 1a is (a) hydrogen; (b) C 1-6 alkyl, optionally substituted with a substituent selected from chloro, cyano, ethoxy, methylthio, (1S,2S,4R)-7,7-dimethylbicyclo[2.2.1]-heptyl, phenyl, chlorophenyl, furanyl, morpholinyl, propionyl, and ethoxycarbonyl; (c) C 2-6 alkenyl, optionally substituted with phenyl; (d) C 3-7 cycloalkyl; (e) C 6-14 aryl, optionally substituted with one or two substituents, each independently selected from fluoro, chloro, cyano, nitro, methyl, trifluoromethyl, ethyl, methoxy, and acetyl; (f) heteroaryl, optionally substituted with one or two methyl; or (g) heterocyclyl.
7. The method of claim 6 , wherein R 1a is (a) hydrogen; (b) methyl, ethyl, propyl, butyl, or pentyl, each optionally substituted with a substituent selected from chloro, cyano, ethoxy, methylthio, (1S,2S,4R)-7,7-dimethylbicyclo[2.2.1]-heptyl, phenyl, chlorophenyl, furanyl, morpholinyl, propionyl, and ethoxycarbonyl; (c) ethenyl or allyl, each optionally substituted with phenyl; (d) cyclobutyl, cyclopentyl, or cyclohexyl; (e) phenyl, optionally substituted with one or two substituents, each independently selected from fluoro, chloro, cyano, nitro, methyl, trifluoromethyl, ethyl, methoxy, and acetyl; (f) furanyl, thienyl, isoxazolyl, pyrazolyl, 1,2,3-thiadiazolyl, pyridinyl, pyrazyl, benzofuranyl, benzo[c][1,2,5]oxadiazolyl, benzothienyl, or benzothiazolyl, each optionally substituted with one or two methyl; or (g) morpholinyl.
8. The method of claim 2 , wherein R 1b is hydrogen or C 1-6 alkyl.
9. The method of claim 8 , wherein R 1b is hydrogen, methyl, or ethyl.
10. The method of claim 2 , wherein R 1c is (a) hydrogen; (b) C 1-6 alkyl, optionally substituted with one, two, or three substituents, each of which is independently selected from cyano, halo, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, heterocyclyl, —C(O)R a , —C(O)OR a , and —SR a , where the cycloalkyl, aryl, heteroaryl, and heterocyclyl are each further optionally substituted with one, two, or three substituents, each of which is independently halo or C 1-6 alkyl; (c) C 1-6 alkenyl, optionally substituted with C 6-14 aryl; (d) C 3-7 cycloalkyl, optionally substituted with one or two C 1-6 alkyl; (e) C 6-14 aryl, optionally substituted with one, two, or three substituents, each of which is independently selected from halo, nitro, cyano, —OR a , —C(O)R a , and C 1-6 alkyl, where the alkyl is further optionally substituted with one, two, or three halo; (f) heteroaryl, optionally substituted with one, two, or three substituents, each of which is independently halo or C 1-6 alkyl; or (g) heterocyclyl.
11. The method of claim 2 , wherein R 1C is (a) hydrogen; or (b) C 1-6 alkyl, C 2-6 alkenyl, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, or heterocyclyl, each optionally substituted with one or two substituents, each of which is independently selected from halo, cyano, nitro, C 1-6 alkyl, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, heterocyclyl, —OR a , —SR a , and —C(O)R a , where R a is as defined herein and the alkyl, cycloalkyl, aryl, heteroaryl, and heterocyclyl are each optionally further substituted with one or two substituents, each of which is independently halo or C 1-6 alkyl.
12. The method of claim 10 , wherein R 1c is (a) hydrogen; or (b) C 1-6 alkyl, C 2-6 alkenyl, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, or heterocyclyl, each optionally substituted with one or two substituents, each of which is independently selected from fluoro, chloro, cyano, nitro, methyl, trifluoromethyl, ethyl, methoxy, ethoxy, methylthio, (1S,2S,4R)-7,7-dimethylbicyclo[2.2.1]-heptyl, phenyl, chlorophenyl, furanyl, morpholinyl, acetyl, propionyl, and ethoxycarbonyl.
13. The method of claim 10 , wherein R 1c is (a) hydrogen; (b) C 1-6 alkyl, optionally substituted with a substituent selected from chloro, cyano, ethoxy, methylthio, (1S,2S,4R)-7,7-dimethylbicyclo[2.2.1]-heptyl, phenyl, chlorophenyl, furanyl, morpholinyl, propionyl, and ethoxycarbonyl; (c) C 2-6 alkenyl, optionally substituted with phenyl; (d) C 3-7 cycloalkyl; (e) C 6-14 aryl, optionally substituted with one or two substituents, each independently selected from fluoro, chloro, cyano, nitro, methyl, trifluoromethyl, ethyl, methoxy, and acetyl; (1) heteroaryl, optionally substituted with one or two methyl; or (g) heterocyclyl.
14. The method of claim 10 , wherein R 1c is (a) hydrogen; (b) methyl, ethyl, propyl, butyl, or pentyl, each optionally substituted with a substituent selected from chloro, cyano, ethoxy, methylthio, (1S,2S,4R)-7,7-dimethylbicyclo[2.2.1]-heptyl, phenyl, chlorophenyl, furanyl, morpholinyl, propionyl, and ethoxycarbonyl; (c) ethenyl or allyl, each optionally substituted with phenyl; (d) cyclobutyl, cyclopentyl, or cyclohexyl; (e) phenyl, optionally substituted with one or two substituents, each independently selected from fluoro, chloro, cyano, nitro, methyl, trifluoromethyl, ethyl, methoxy, and acetyl; (f) furanyl, thienyl, isoxazolyl, pyrazolyl, 1,2,3-thiadiazolyl, pyridinyl, pyrazyl, benzofuranyl, benzo[c][1,2,5]oxadiazolyl, benzothienyl, or benzothiazolyl, each optionally substituted with one or two methyl; or (g) morpholinyl.
15. The method of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each independently hydrogen, halo, or C 1-6 alkyl.
16. The method of claim 15 , wherein two of R 1 , R 2 , R 3 , R 4 , and R 5 are halo or C 1-6 alkyl, and the remaining three are hydrogen.
17. The method of claim 15 , wherein two of R 1 , R 2 , R 3 , R 4 , and R 5 are chloro or methyl, and the remaining three are hydrogen.
18. The method of claim 17 , wherein R 1 , R 3 , and R 5 are hydrogen, and R 2 and R 4 are chloro or methyl.
19. The method of claim 18 , wherein R 2 and R 4 are chloro.
20. The method of claim 18 , wherein R 2 and R 4 are methyl.
21. The method of claim 17 , wherein R 2 , R 3 , and R 5 are hydrogen, and R 1 and R 4 are chloro or methyl.
22. The method of claim 21 , wherein R 1 and R 4 are chloro.
23. The method of claim 21 , wherein R 1 and R 4 are methyl.
24. The method of claim 1 , wherein R 6 is cyano or nitro.
25. The method of claim 1 , wherein R 7 is C 1-6 alkyl.
26. The method of claim 1 , wherein m is 1.
27. The method of claim 1 , wherein n is 1 or 2.
28. The method of claim 1 , wherein p is 0.
29. The method of claim 1 , wherein X is O.
30. The method of claim 1 , wherein X is S.
31. The method of claim 1 selected from the group consisting of:
and enantiomers, mixtures of enantiomers, mixtures of two or more diastereomers, tautomers, and mixtures of two or more tautomers thereof; and pharmaceutically acceptable salts, solvates, hydrates, and prodrugs thereof.
32. The method of claim 1 , wherein the compound is a hydrochloride salt.
33. The method of claim 1 , wherein the disorder, disease, or condition is asthma, exercise induced asthma, allergic rhinitis, atopic dermatitis, chronic obstructive plumonary disease, or allergic conjunctivitis.
34. The method of claim 1 , wherein the compound is administered orally, parenterally, or topically.
35. The method of claim 1 , wherein the compound is administered in combination with a second therapeutic agent.
36. A method for modulating CCR3 activity, comprising contacting a CCR3 receptor with the compound of Formula I:
or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, a tautomer, or a mixture of two or more tautomers thereof; or a pharmaceutically acceptable salt, solvate, hydrate, or prodrug thereof;
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently (a) hydrogen, halo, cyano, nitro, or guanidine; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; or (c) —C(O)R 1a , —C(O)OR 1a , —C(O)NR 1b R 1c , —C(NR 1a )NR 1b R 1c , —OR 1a , —OC(O)R 1a , —OC(O)OR a1 , —OC(O)NR 1b R 1c , —OC(═NR 1a )NR 1b R 1c , —OS(O)R 1a , —OS(O) 2 R 1a , —OS(O)NR 1b R 1c , —OS(O) 2 NR 1b R 1c , —NR 1a R 1b , —NR 1a C(O)R ld , NR 1a C(O)OR 1d , —NR 1a C(O)NR 1b R 1c , —NR 1a C(═NR 1d )NR 1b R 1c , —NR 1a S(O)R 1d , —NR 1a S(O) 2 R 1d , —NR 1a S(O)NR 1b R 1c , —NR 1a S(O) 2 NR 1b R 1c , —SR 1a , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c ;
R 7 is (a) halo, cyano, nitro, oxo, or guanidine; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; or (c) —C(O)R 1a , —C(O)OR 1a , —C(O)NR 1b R 1c , —C(NR 1a )NR 1b R 1c , —OR 1a , —OC(O)R 1a , —OC(O)OR 1a , —OC(O)NR 1b R 1c , —OC(═NR 1a )NR 1b R 1c , —OS(O)R la , —OS(O) 2 R 1a , —OS(O)NR 1b R 1c , —OS(O) 2 NR 1b R 1c , —NR 1b R 1c , NR 1a C(O)R 1d , —NR 1a C(O)OR 1d , —NR 1a C(O)NR 1b R 1c —NR 1a C(═NR 1d )NR 1b R 1c , —NR 1a S(O)R 1d , —NR 1a S(O) 2 R 1d , —NR 1a S(O)NR 1b R 1c , NR 1a S(O) 2 NR 1b R 1c , —SR 1a , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1c , or —S(O) 2 NR 1b R 1c ;
X is O or S;
R Ya is —C(O)R 1a , —C(O)OR 1a , —C(O)NR 1b R 1c , —C(S)NR 1b R 1c , —C(S)NR 1a C(O)NR 1b R 1c , —C(NR 1a )NR 1b R 1c , —C(NNO 2 )NR 1b R 1c , —S(O)R 1a , —S(O) 2 R 1a , —S(O)NR 1b R 1e , or —S(O) 2 NR 1b R 1c ; with the proviso that R Ya is not —C(O)O-t-butyl;
m is an integer from 0 to 3;
n is an integer from 1 to 3;
p is an integer from 0 to 4; and
each R 1a , R 1b , R 1c and R 1d is independently hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, heteroaryl, or heterocyclyl; or each pair of R 1b and R 1c together with the N atom to which they are attached independently form heteroaryl or heterocyclyl;
with the proviso that the compound is not 4-(2-(3,5-dimethylphenoxy)-5-nitrophenylsulfonyl)piperazine-1-carbaldehyde; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heterocyclyl, and heteroaryl is optionally substituted with one or more groups, each independently selected from (a) cyano, halo, and nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, and heterocyclyl, each optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Q; and (c) —C(O)R a , —C(O)OR a , —C(O)NR b R c , —C(NR a )NR b R c , —OR a , —OC(O)R a , —OC(O)OR a , —OC(O)NR b R c , —OC(═NR a )NR b R c , —OS(O)R a , —OS(O) 2 R a , —OS(O)NR b R c , —OS(O) 2 NR b R c , —NR b R c , —NR a C(O)R d , —NR a C(O)OR d , —NR a C(O)NR b R c , —NR a C(═NR d )NR b R c , —NR a S(O)R d , —NR a S(O) 2 R d , —NR a S(O)NR b R c , —NR a S(O) 2 NR b R c , —SR a , —S(O)R a , —S(O) 2 R a , —S(O)NR b R c , and —S(O) 2 NR b R c , wherein each R a , R b , R c , and R d is independently (i) hydrogen; (ii) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl, each optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Q; or (iii) R b and R c together with the N atom to which they are attached form heterocyclyl, optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Q;
wherein each Q is independently selected from the group consisting of (a) cyano, halo, and nitro; (b) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, and heterocyclyl; and (c) —C(O)R e , —C(O)OR e , —C(O)NR f R g , —C(NR e )NR f R g , —OR e , —OC(O)R e , —OC(O)OR e , —OC(O)NR f R g , —OC(═NR e )NR f R g , —OS(O)R e , —OS(O) 2 R e , —OS(O)NR f R g , —OS(O) 2 NR f R g , —NR f R g , —NR e C(O)R h , —NR e C(O)OR h , —NR e C(O)NR f R g , —NR e C(═NR h )NR f R g , —NR e S(O)R h , —NR e S(O) 2 R h , —NR e S(O)NR f R g , —NR e S(O) 2 NR f R g , —SR e , —S(O)R e , —S(O) 2 R e , —S(O)NR f R g , and —S(O) 2 NR f R g ; wherein each R e , R f , R g , and R h is independently (i) hydrogen; (ii) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6-14 aryl, C 7-15 aralkyl, heteroaryl, or heterocyclyl; or (iii) R f and R g together with the N atom to which they are attached form heterocyclyl.Cited by (0)
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